ANNUAL & UPCOMING EVENTS in Middlebury
All year long, Middlebury is home to great events planned by local businesses and organizations, many of which are free or low-cost. Outdoor concerts, markets, parades, holidays festivities, a food truck festival…these are all events you can experience for yourself right here in Middlebury every year. Check them out!
All Year Round
First Fridays
Middlebury businesses are excited to keep their doors open late on the First Friday of each month!
Middlebury Farmers Market
All year round Saturdays 9.00am-12.30pm 530 Exchange St Middlebury
Spring/Summer 2026
Midd Summer Markets
The Midd Summer Markets will be under new management starting in 2026. Offering a consistent weekly schedule on Triangle Park every THURSDAY from 3:00 PM to 7:00 PM, June – August. [Note, that there will be no MSM market on 7/16, as that week is Festival on the Green.] In addition to Thursday markets, select Saturday market dates will be offered between May and September from 10AM – 2PM.
Addison County Farmers Market
Join in every Wednesday June – Oct from 1:30 PM to 6:00 PM on the Middlebury Town Green for the Addison County Farmers Market — a weekly celebration of community, connection, and the incredible bounty of Vermont’s farms and food producers. 1 Merchant’s Row.
Memorial Day Parade
Hosted by the American Legion May 25
Mid June. Middlebury comes alive with artists at scenic spots around town—parks, river overlooks, sidewalks, and gardens—capturing the beauty of Vermont on the spot.
Foodaroo
Food truck festival featuring live entertainment hosted by Middlebury Underground
Festival on the Green
A week-long free concert series on the town green
St Stephen’s Peasant Market
The area’s largest flea market and rummage sale
Lion’s Club Auction
Auction and BBQ on the green
Middlebury New Filmmakers Festival
A four-day event celebrating new filmmakers
Fall
Middlebury Car Show and Fall Festival
An event co-hosted by the BMP and the Addison County Chamber of Commerce
Middlebury Maple Run
Vermont’s Sweetest Half Marathon, 10K & 5k run
Kelly Brush Ride
Annual cycling fundraiser for the Kelly Brush Foundation, supporting adaptive sports
ACORN Tour de Farms
Casual cycling tour of Addison County farms
Middlebury Pride
Inclusive and family-friendly parade down Main St, followed by a festival in the green!
Spooktacular
Trick-or-Treating down Main Street
Winter
Very Merry Middlebury
A month-long celebration of the holidays, including Midd Night Strolls with extended evening shopping, tasting and strolling
Love Middlebury
February heart hunt in downtown Middlebury.
Follow Better Middlebury Partnership on Facebook and @experiencemiddlebury on Instagram for our most up-to-date information on local events not to miss!